Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs

Ciaran Paul Seath, James W. B. Fyfe, John J. Molloy, Allan J. B. Watson

Research output: Contribution to journalArticle

7 Citations (Scopus)
56 Downloads (Pure)

Abstract

The synthesis of functionalized oxindoles and benzofuranones via oxidation of 2-BMIDA indoles and benzofurans, respectively, is described. Interconversion of boron species (BMIDAàBF3K) was necessary to enable oxidation and overcome boronic acid stability issues associated with a difficult BMIDA hydrolysis. Overall, a robust process was developed that allowed access to a small library of oxindole and benzofuranone products and facilitated the step-efficient synthesis of biologically-active compounds containing the oxindole pharmacophore.
Original languageEnglish
Number of pages7
JournalSynthesis
Early online date12 Aug 2016
DOIs
Publication statusE-pub ahead of print - 12 Aug 2016

Keywords

  • boron
  • oxidation
  • heterocycles
  • lactams
  • lactones
  • functionalized oxindoles synthesis
  • benzofuranones
  • boronic acid stability
  • oxindole pharmacophore

Fingerprint Dive into the research topics of 'Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs'. Together they form a unique fingerprint.

  • Cite this